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Direct cyclopropanation of activated N-heteroarenes via site- and stereoselective dearomative reactions

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Abstract

A divergent cyclopropanation reaction has been accomplished via the dearomative addition of sulfur ylides to activated N-heteroarenes. A series of biologically significant molecular skeletons was obtained by the direct cyclopropanation of quinolinium zwitterions. Furthermore, a straightforward synthetic route to optically enriched cyclopropane-fused heterocycles was developed using sulfur ylides as chiral nucleophiles in the 1,4-dearomative reaction.

Graphical abstract: Direct cyclopropanation of activated N-heteroarenes via site- and stereoselective dearomative reactions

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Article information


Submitted
17 Dec 2019
Accepted
30 Dec 2019
First published
10 Jan 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Direct cyclopropanation of activated N-heteroarenes via site- and stereoselective dearomative reactions

J. Lee, D. Ko, H. Park and E. J. Yoo, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC06369B

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